Flavored tobacco composition

ABSTRACT

8,13 : 13,20-Diepoxy-15,16-dinorlabdane is disclosed as being a useful ingredient in flavouring compositions for the aromatization of tobacco products.

Umted States Patent 11 1 [111 3,

Dietrich Oct. 28, 1975 [54] FLAVORED TOBACCO COMPOSITION [75] Inventor: Paul Dietrich, Chene-Bourg, [56] References C'ted Geneva, S it e l d UNITED STATES PATENTS [73] Assigneez Firmenich SA, Geneva Switzerland 3,840,023 10/1974 Demole 131/144 Filed J 28 1975 FOREIGN PATENTS OR APPLICATIONS 338,469 7 1959 Switzerland 260/3405 21 Appl. No.: 544,711

Primary Examiner-Melvin D. Rein ig App Data AttOrne), Agent, or Firm-Pennie & EdmOrIdS FED. I2, Switzerland 521 U.S. Cl. 131/17 R- 131 144 8113 I32O'DiePmY'Iimdinmlabdane is dislsed 51 1m. (:1. A24B 3/12; A2413 15/04 as being a useful ingredient in fla ouring compositions [58] Field of Search 260/3405, 346.1; 426/221; ammatizatm Of Pmducts' 1 FLAVORED TOBACCO COMPOSITION DESCRIPTION OF THE INVENTION This invention relates to a flavouring composition for the aromatization of tobacco or tobacco-substitute products, comprising as one of its ingredients a compound having the formula The said compound is defined as 8,13 13,20- diepoxy-15,16-dinorlabdane. This invention relates further to a process for improving, enhancing or modifying the organoleptic properties of tobacco and tobacco products, which comprises vadding thereto a small but effective amount of the compound of formula (I).

The present invention also relates to a tobacco or tobacco-substitute article comprising as flavourmodifying ingredient a small but effective amount of the compound of formula (I).

BACKGROUND OF THE INVENTION tives to these tobacco mixtures to further enhance the organoleptic properties thereof.

We have now surprisingly found that theflavour and taste of tobacco products could be particularly enhanced and improved by the addition thereto of small amounts of the compound of formula (I).

PREFERRED EMBODIMENTS OF THE INVENTION The compound of formula (I) can be used on its own,

' or in compositions comprising one or more other flavouring or odoriferous ingredients. The compound and compositions of the invention may be used in a variety of forms, depending upon their chemical nature, solubility and stability, but they are preferably used in solution. For the flavouring of tobacco, they are preferably added after ageing, curing and shredding, but before the tobacco is formed into cigarettes or other finished products. A convenient method for flavouring tobacco consists in spraying it with a solution of the flavouring compound or composition in alcohol, or in a mixture of alcohol and propylene glycol.

The compound of formula (I), whenever used in accordance with the invention, can develop a distinct woody, amber-like character. These properties are particularly developed on smoking the tobacco.

The proportion in which the flavouring agent of the invention is used in flavouring compositions or is added to tobacco can vary widely, depending upon the specific organoleptic effect it is desired to achieve and the type of tobacco to which it is added. Interesting flavour effects can be achieved with amounts ranging from 0.01 to 10 parts per million (ppm), preferably from 0.1 to 5 ppm and most preferably from 0.5 to 2 ppm, based on the weight of the product flavoured. Similarly, when used as a flavouring ingredient in a flavour composition, the proportion of compound (I) can vary within a wide range and being comprised between about 10 and 20%, based on the weight of the flavouring composition.

In all cases, the ranges mentioned can be varied, in order to achieve specific flavouring effects.

The compound of formula (I) is a polycyclic ketal whose structure was first determined by Ruzicka and Jeger see namely Swiss Pat. No. 338,469 and Helv.- Chim.Acta, 37,543 (1954). Its olfactive properties were mentioned in the above said references and its utility in the perfumery was recognized ever since then.

So far, however, no mention nor suggestion have been put forth concerning its possible usefulness in the field of flavouring.

Compound (I) can be prepared in accordance with known synthetic procedures viz. described in the above cited Swiss patent and in its pure form it occurs as a crystallin solid having a melting point at about 1 17C.

Due to the simultaneous presence of several chirality centres in its molecule, compound (I) comprises several racemic or optical active stereoisomers. It has to be understood, however, that for all practical purposes isomeric mixtures, such as those directly obtained by the known cited syntheses, are preferably used.

The invention is better illustrated by, but not limited to the following Example.

EXAMPLE 100 g of American blend tobacco were sprayed with 1 g of a 0.001% solution of 8,13 13,20-diepoxy- 15,16-dinorlabdane in ethanol, and the tobacco thus flavoured was used to manufacture test cigarettes. As a control, cigarettes were also manufactured from the same tobacco sprayed with 95% ethanol alone. The smoke from the cigarettes was subjected to organoleptic evaluation by a panel of flavour experts, who unanimously stated that the smoke of the flavoured cigarettes possessed a typical and pleasant woody and amber-like flavour character.

What I claim is:

1. A process for improving, enhancing or modifying the organoleptic properties of tobacco and tobacco products, which comprises adding thereto a small but effective amount of a compound having the formula 2. A tobacco or tobacco-substitute article having added thereto a small but effective amount of a compound having the formula said compound being effective to enhance the organoleptic properties of the article.

UNITED STATES PATENT AND TRADEMARK OFFICE CERTIFICATE OF CORRECTION PATENT NO. 3,915,175

DATED October 28, 1975 INV ENTOR(S) Paul Dietrich It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:

Column 2, line 44, "0.001" should read 0.0l--.'

Signed and Sealed this ninth D3) Of March 1976 [SEAL] Attest.

RUTH C. MASON C. MARSHALL DANN Atlextr'ng Officer Commissioner ofParems and Trademarks 

1. A PROCESS FOR IMPROVING, ENHANCING OR MODIFYING THE ORGAOLEPTIC PROPERTIES OF TOBACCO AD TOBACCO PRODUCTS WHICH COMPRISES ADDING THERETO A SMALL BUT EFFECTIVE AMOUNT OF A COMPOUND HAVING THE FROMULA
 2. A tobacco or tobacco-substitute article having added thereto a small but effective amount of a compound having the formula 